Modified Strigolactone Derivatives for Plant Growth Regulation
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Solution Overview
Problem
Strigolactone derivatives with modifications to the butenolide ring often result in loss of activity for plant growth regulation and seed germination, as the hydrolysis of the butenolide group affects their interaction with plant receptors, leading to reduced efficacy in controlling parasitic weed germination and plant architecture.
Innovation Solution
Development of novel heterocyclic derivatives with specific modifications to the butenolide ring, such as compounds of Formula (I), which retain biological activity by maintaining interaction with plant receptors like D14 and SLR1, thereby controlling plant growth and seed germination effectively.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If the butenolide ring of strigolactone is modified, then the chemical structure is improved for potential enhanced activity, but the biological activity is lost due to inability to interact with plant receptors
Solution Approach 1:
The patent applies parameter changes by systematically modifying the butenolide ring structure with various heterocyclic groups (pyrrolidinone, oxazolidinone, thiazolidinone, etc.) while maintaining the core strigolactone framework. These structural parameter changes were made to explore structure-activity relationships and identify modifications that preserve biological activity despite ring alterations
Solution Approach 2:
The patent creates composite molecular structures by combining the strigolactone core with various heterocyclic ring systems. These composite structures integrate the known active pharmacophore with modified ring systems to achieve both structural improvement and retention of biological activity through careful design of the hybrid molecular architecture
2Reliability
If the butenolide group is hydrolysed by D14 receptor, then the interaction mechanism is activated, but the biological efficacy is reduced leading to loss of plant growth regulation
Solution Approach 1:
The patent applies preliminary action by pre-modifying the butenolide ring with heterocyclic groups before the compound encounters the D14 receptor in planta. This pre-modification aims to create compounds that will resist hydrolysis or maintain activity after hydrolysis, thereby preserving biological efficacy while still allowing receptor interaction to occur
Solution Approach 2:
The patent inverts the conventional approach by instead of modifying the butenolide ring to enhance activity (which leads to hydrolysis and loss of activity), the modification is designed to maintain stability against hydrolysis while preserving the ability to interact with the D14 receptor and SLR1 protein, thus reversing the typical structure-activity relationship outcome
3Object-affected harmful factors
If strigolactone derivatives are used to control parasitic weed germination, then the agricultural benefit is achieved, but the structural modifications cause loss of seed germination promotion
Solution Approach 1:
The patent applies local quality by making specific localized modifications to the butenolide ring region of the strigolactone molecule while leaving the rest of the molecular structure intact. This localized modification approach allows the compound to maintain its ability to promote seed germination through the intact core structure while the modified ring provides resistance to hydrolysis and maintains parasitic weed control activity
Data Source
AI summary
The present invention relates to novel heterocyclic derivatives of Formula (I), to processes and intermediates for preparing them, to plant growth regulator and seed germination promoting compositions comprising them and to methods of using them for controlling the growth of plants and/or promoting the germination of seeds.